


The Five Shitty Dates of Jemmy Madison

by thebureauisclosed (insibbegerest)



Series: Acing High School [4]
Category: Hamilton - Miranda
Genre: Alternate Universe - High School, Alternate Universe - Modern Setting, Aromantic, Aromantic Characters, Asexual Character, Bad Matchmaking, Friendship, Gen, Humor, Texting
Language: English
Status: Completed
Published: 2016-04-03
Updated: 2016-04-03
Packaged: 2018-05-31 01:35:06
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,938
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6450160
Author URL: https://archiveofourown.org/users/insibbegerest/pseuds/thebureauisclosed
Summary: <blockquote class="userstuff">
              <p>Thomas could be an oblivious idiot, but there was at least one upside to his dumb ideas; James got to meet Dolley.</p>
            </blockquote>





	The Five Shitty Dates of Jemmy Madison

**1.**

"You... what?"

"I am a satanist," James said, sporting a face that would win him a fortune in poker. "I like to sacrifice animals once in a while. After that, I usually bury them in my garden. I hope it's not a problem."

The girl looked him up and down, her eyes filling with terror. James knew he wasn't the scariest looking guy, but he had some hope that the black clothes, solemn voice and evil looks would give his fables at least some credibility.

She rose up to her feet so quickly she almost knocked over the chair she'd been sitting on. "I... I think.. I have to go," she stammered and ran for the door.

James sighed. He felt a weird mix of pity and satisfaction. It didn't give him any joy to frighten the poor girl like that, but... Hey, he let her finish her dinner and paid the bill, so at least she'd have a full stomach and a story to tell.

* * *

 

"It didn't work out?" Thomas, who had no inkling about what had happened in the restaurant, looked genuinely baffled.

James shook his head, "It didn't, no... She left after about five minutes."

Thomas, who was taking this more personally than James, gritted his teeth, "Jesus, what a bitch."

"Language, Thomas," James reminded him, calm but firm. No bitches, fags and the like were allowed in the vicinity of James Madison.

"But... you're so intelligent and polite and funny and... " Thomas coughed awkwardly, "you're not ugly, either. No homo."

James overcame the urge to roll his eyes so hard they'd pop out of his head, offering Thomas a kind smile instead, "Despite what you might believe, I'm not perfect. I can't and I don't expect everyone to like me. Apparently I wasn't this girl's type, stuff like that happens, no need for anyone to get mad at her." Anyone meaning Thomas.

"See, this is exactly what I'm talking about!" Thomas exclaimed. "She dumped you and yet here you are all reasonable and positive and standing up for her. Trust me, whichever girl scores you one day will consider herself lucky."

Very lucky indeed. Boys, who see dirty activities as a waste of time and aren't sure what having a crush even means (He thinks he might have had a crush once? Or maybe not? He's confused), have always been in high demand, after all.

* * *

 

This was the story of how Thomas Jefferson had arranged a date for James for the first time. The dummy had actually believed he'd been doing James a favor, ugh. However, it had been impossible to say no to Thomas' bright smile when he'd approached James, exclaiming he'd found just the perfect girl for him.

The second James agreed to go along with it, he also decided he would fuck up the date so magnificently that Thomas would abandon his efforts to find him a datemate.

And even if it didn't work this time, well... James was a quick thinker, he believed he could get himself out of another unwanted dinner just as easily.

 

**2.**

"Hallo, ich heiße James. Und du?"

"Uh... Sorry?"

"Verstehst du mich nicht? Ich spreche kein Englisch."

"What? You don't speak English?"

James made a confused face, "Wie bitte?"

"...nevermind, I think I gotta go..."

As the girl was angrily marching away, James could hear her mutter under her breath, "What the hell was Jefferson thinking..."

 

**3.**

"Uh, James?"

"Yes, Thomas?"

"What are you doing in our living room?"

James looked up at Thomas, then back at the book he had been reading. "Why, taming dragons, obviously."

"Okaay, let me rephrase the question," Thomas sighed, hopping onto the pink sofa right next to James, "why aren't you with Emily?"

"Emily?" James' nose scrunched up in confusion before he realized what the hell this was all about. Oh. He'd promised Thomas he would go on another one of those arranged dates today, but he had forgotten, having too much fun with the latest book he'd stolen from Thomas' gigantic library to think about anything else.

"Yes, Emily," Thomas repeated, this time louder. "Y'know, the lovely girl who was dying to meet you and you obviously ... didn't bother to show up."

"I am sorry."

Thomas sighed, "Well, I guess it doesn't matter anymore." He bent his head down to take a look at the cover of James' book. "Good Omens, huh? Great choice. I've read that one three times already."

"I know," the corner of James' lip twitched, "you wouldn't stop talking about it. Why do you think I picked it up?"

Thomas shifted closer to James and made himself comfortable by laying his head on his friend's shoulder. "I'll just sit here and read with you," he said and glanced down at the pages, "I have nothing better to do anyway."

"You could watch The Big Bang Theory, as you do almost every evening."

"I thought you hated it."

"It's not one of my favorites, that's true," James replied diplomatically.

"I'm not in the mood for TV," Thomas said.

James didn't comment on that. Although he enjoyed his conversations with Thomas, now it was reading time during which no unnecessary speaking was allowed. He gave a short nod to show Thomas he'd heard his words and then he turned the page.

They stayed like that for countless minutes, side by side, engrossed in the same story. Thomas burst into laughter on a regular basis, he even read some of his favorite parts aloud. Had it been anyone else, James would have killed them for this kind of behavior; he didn't really mind when it came to Thomas, though. Besides, this was Thomas' place and Thomas' book and James thought that taking someone's life because they dared read their own book in their own house might be considered something of an overreaction.

But of course, Thomas Jefferson had to ruin the moment because that's what Thomas Jefferson does. "Hey, James?"

"Mmm?"

"Why are you afraid of being with someone?"

James snorted. Right, because his unwillingness to go on dates with random people had to do with him being scared of love. "I'm not afraid, I just... don't care much about romance."

"Did someone hurt you?"

"You're hurting me right now with all your questions."

Thomas threw his hands in the air, "Come on, I'm trying to help."

Well, you aren't helping at all. "I don't think relationships are as important as people make them out to be... Can we leave it at that, please?" James looked at Thomas and he instantly regretted the decision, because the last thing he needed to see was the pity plainly written in Thomas's face.

"You haven't found the right one, that's all," Thomas muttered in what he probably hoped was a soothing manner, but it only served to make James want to shove the book up his nostril.

Nah, not really. He loved literature too much to commit such an atrocity.

 

**4.**

This time, Thomas had picked a guy. James was almost impressed that the thought had occurred to Thomas that his best friend might not be exactly straight.

If only he hadn't gone about it the wrong way, though.

"I'm sorry, this isn't your fault... You're really handsome and everything," James said with an awkward smile - and he wasn't lying, the boy's face was a piece of art, "but I don't swing that way."

The boy sighed, "Shit, not this again... Why would Jefferson even try to set us up, then?"

James laughed, "Because he's oblivious as hell."

 

**5.**

The girl was gorgeous. Not gorgeous enough to give James mushy feelings, obviously, but still gorgeous. With her huge brown eyes, perfectly done make up and preppy clothes, she looked like a movie star. What the hell was Thomas thinking, setting him up with someone so out of his league?

Well, perhaps he wouldn't have to come up with any excuses this time; as soon as he approaches her in his crumpled white shirt and old jeans, she'll likely dump him before he gets to say hello.

James sighed and walked up to her table. His date was too busy staring at her phone to notice him, though. After he had spent several awkward seconds waiting for her to acknowledge his presence, James had to clear his throat in order to get her attention. "Hey," he said.

Finally, she looked up. "Oh, hello! Sorry, I didn't see you coming." James couldn't blame her for overlooking him, he knew how entirely unremarkable he was.

They shook hands; her squeeze was short but firm. "Name's Dolley Payne, nice to meet you."

"James Madison. Likewise." He gave her a polite smile and sat down, his mind already in the process of fabricating a new fake story that would  scare Dolley off.

"James is too... I don't know, boring. Don't you have a nickname? Something ridiculous like... Jimmynator? The grand Jay?"

"Jimmynator," James repeated slowly. "Seriously?"

In lieu of a response, Dolley just giggled.

"No, I don't have a nickname, James will have to do. Sorry to disappoint."

"I know a James already," Dolley mused. "Also a Jim, Jimmy, Jamie, Jamey, JJ, Jimbo... I'll call you Jemmy." It wasn't a question, just a simple statement that allowed no further discussion.

"Yeah, alright." There was no point in arguing, it wasn't like he'd see her again after he fucks up their 'date'. And while Jemmy sounded weird, he didn't really care.

And honestly? He liked weird.

"Good." Dolley smiled and shifted slightly on her seat. "Listen Jemmy, before we begin, there's something you should know."

 "Okay?" Good, let the girl talk – that would buy him some time to figure out what to do.

"No kissing or holding hands before marriage. You have to convert to my faith because my parents are very religious. I use Internet Explorer. I have nine younger siblings I have to take care of, work three side jobs, I sing in a death metal band and visit strip clubs every other evening, which means I have very little free time. I couldn't go on dates with you more often than... once every three months. And I might cheat on you. How does all that sound to you?"

James blinked once. Twice. Three times. He had no idea how to react. Dolly had rendered him utterly speechless. "T-that's... uh," he stuttered out eventually. "I mean... Internet Explorer? Really?"

"Problem?"

Wait... Bullshitting his dates until they've had enough? That was his area, and yet, Dolley had beaten him to it. What were her intentions? Was she testing him, or simply showing she wasn't interested? He was hoping for the latter to be true. "You know, Dolley, if you don't like me, you can just say it. I'm a big boy, I won't cry."

That answer seemed to  have surprised her. "Oh, it's not that I don't like you, you're cute!" Shit. "I just don't... like like you."

...not shit?

James' mouth split into a wide grin, "I don't like like you either."

"Thank God!" Dolley clasped her hands in relief. "I just hate dating so much."

"It's pretty overrated, yeah. Can't say I hate it, but... I prefer staying single."

"Bad experience?" He was praying to god Dolley wouldn't pull the 'who hurt you' thing that he hated so much.

"Not exactly. It's just... who I am."

"Could it be that... nah."

"Could it be that what?" James asked.

"Have you ever heard of aromanticism?"

Holy crap, did that mean Dolley was... What were the fucking chances of two aros meeting on a date? Now that was a textbook example of irony. For a split second he almost regretted he wasn't out to Thomas because this was an experience worth sharing.

Dolley frowned at him, "Why the hell are you smiling? What's funny?"

"I'm sorry, it's just..." James couldn't stop smiling no matter how much he was trying, "I'm gray aro."

That made Dolley laugh, "Are you kidding me? That's great! I am so aro it hurts."

"So why'd you agree to go on a date with me?" He was aware some aros didn't mind dating, but... Dolley appeared to be the 'Touch me and die' kind of aro.

She rolled her eyes, "Burr insisted. Now that he's with Theodosia, he thinks that relationships are the best thing ever. He wouldn't stop convincing me to give it a go, so I agreed, although not too excitedly. He said that even if I don't find love, I'll almost certainly get laid, so it's a win win."

James made a weird sound somewhere between a cough and a laugh, "Yeah, uh, I doubt that, sorry. Everything related to sex seems really boring to me, I'd be an awful fuckbuddy."

"Are you also ace, then?"

James nodded. Wow, he'd never told anyone else about this and here he was now, discussing his orientation with someone he barely knew. And in spite of him not trusting people easily most of the time, he felt like he could trust her. She understood, after all.

"I'm hetero, I guess. Sex is fine, but I'm getting tired of guys always wanting more." Dolley made a face. "Just because I fuck them doesn't mean I want to hold hands and cuddle and marry them one day."

James nodded again. This wasn't quite his area of expertise and he didn't know how to react without embarrassing himself.

"Ah, sorry... Am I making you uncomfortable?" Dolley asked, slight worry tinting her low and pleasant voice.

"Not really, I just... um... this isn't something I have experience with," he explained, laughing nervously. "And I... sometimes suck at talking to people. I'm sorry."

Dolley smiled, "Aw, that's adorable. Listen, Jemmy... I'll have to leave you, I made some plans for tonight because I honestly wasn't expecting this date to last more than thirty seconds. The 'no kissing' part of my speech usually does it, the really weak ones panic even before I open my mouth. Either they're intimidated by my beauty or the hijab scares them, whatever. What I want to say is, you're a special case and I'd like to stay in touch, if you agree. You seem nice and I could always use a friend."

"That would be great," James replied. And he meant it - introverted or not, he loved getting to know like-minded individuals.

"Cool!" She took her lipstick out of her handbag, grabbed a napkin and scribbled her number down. "Give me a call when you're in the mood for another friend-date, okay?"

"Okay."

As James was watching her leave, he couldn't tell if he was feeling more amused or confused. Either way, this evening turned out to be much more interesting than he'd hoped.

He stood up, a small smile forming on his face.

* * *

 

(9:37) jmads2766: hello, Dolley

(9:38) Dolololley: hey there Louis Armstrong

(9:40) jmads2766: just wondering – were any of those things you told me about yourself true? except for you being aro

(9:43) Dolololley: I actually have 9 siblings

(9:44) Dolololley: except there is 6 of them, not 9

(9:44) Dolololley: and they aren't siblings, they're my pet spiders <3

(9:47) jmads2766: in that case I also have nine siblings… except there is four of them, they're cats and they officially belong to the Jeffersons

(9:51) jmads2766: one of them doesn't like me, though :/ she will only let Thomas pet her

(9:52) Dolololley: you can always pet my spiders ;)

(9:53) jmads2766: …

(9:56) jmads2766: I… think I'll pass

(10:01) Dolololley: sissy

* * *

 

(2:14) MacAndBees: How did things go with Dolley yesterday??

(2:18) jmads2766: she doesn't find me attractive but she wants to be friends

(2:20) MacAndBees: That sucks… Sorry, bro :o((

(2:21) MacAndBees: You have the worst luck…

(2:26) jmads2766: actually… Thomas?

(2:28) MacAndBees: Yea?

(2:31) jmads2766: can you please… not do this matchmaking thing anymore?

(2:32) jmads2766: I know you want to help but… it's just… I've told you several times I'm not interested in seeing anyone right now and… you keep trying to change my mind

(2:33) jmads2766: that's not what friends do

(2:37) jmads2766: I like being single, ok? It doesn't mean that I'm lonely/weird etc, it's just who I am… I wish you could accept it…

(2:43) MacAndBees: Are you saying… I am not your friend anymore?

(2:44) MacAndBees: Fuck

(2:44) MacAndBees: I am s

(2:45) MacAndBees: Shit sorry I pressed enter too earlx

(2:45) MacAndBees: erly*

(2:45) MacAndBees: eARLY!!!

(2:47) MacAndBees: I amm so sorry is what I was trfying to say

(2:47) MacAndBees: AM* TRYNG*

(2:47) jmads2766: oh my god Thomas please calm down

(2:48) MacAndBees: *TRYING

(2:48) jmads2766: of course you are my friend

(2:49) jmads2766: it's ok I am not mad at you, just… don't do this kind of stuff again, ok?

(2:50) jmads2766: just say 'ok' and we can put this all behind us

(2:50) MacAndBees: Ok

(2:53) MacAndBees: I am really sorry I didn't meant to upse you or make you uncomfortable

(2:54) MacAndBees: Also sorry you know my spellign sucks when I get anxious

(2:55) jmads2766: yes I know… please don't feel bad? you've made a mistake, you apologized, I am not angry and we're still best friends… everything is alright

(2:56) jmads2766: :)

(2:59) MacAndBees: Ok thank you…

(3:04) MacAndBees: Today, 7pm, my place? I'll get us something to eat and we can watch a movie

(3:06) MacAndBees: As an apology?

(3:07) jmads2766: deal! :)

**Author's Note:**

> I know it took me a while to update, sorry about that and thank you for reading!  
> I'll likely write some more stories set in this universe because I'm having so much fun writing about my ace and/or aro children, so... stay tuned :) My tumblr is acelaurens if someone wants to talk or cry about Hamilton or anything of the sort  
> And remember - your identity and your feelings are valid and I root for you!
> 
> (By the way - there's a hidden joke in James' messenger nickname! hint: it has to do with numeral systems)


End file.
